Plastics containing cellulose acetate



Patented Mar. 24, 1925.

PATIENT, OFFICE.

HENRY DREYFUS, OF LONDON, ENGLAND.

PLASTICS CONTAINING GELLULOSE ACETATE.

No Drawing. Original application filed August 5, 1920, Serial No. 401,380. PatentNo. 1,501,206, dated July 15, 1924. Divided and this applicationfiled March 13, 1923. Serial No. 624,806.

.To all whom it may concern:

Be it known that I, IIENRY DRnYrUs, a citizen of the Swiss Republic, residing at London, England, have invented certain new and useful Improvements in Plastics Containing Cellulose Acetate, of whichthe following is aspecification, I i This invention, relates fto'the hmanufacture "of vsolutions, celluloid-like, masses, films, dopes, artificialsilk-or other compositions, preparations or articles v (hereinafter included in they term compositionslof mat ter) having a basis of cellulose'acetate, and is characterized by the employment or application of certain new or improved high-boiling solvents or plasticizing agents in and for such solutions, compositions, preparations or products hereinafter and in the claiming clauses included in the term composition of matter.

In addition-to the volatile solvents or diluents, such for instance as acetone, alcoholbenzene mixtures, methyl acetate and so especially the case for uses where the solutions, compositions or preparations are exposed to low temperatures in service, as in the case of aircraft dopes,outdoor coatings and so forth. Also the high boiling solvents must be insoluble or very little soluble in water.

In the specification of a previous U. S. Patent No. 1,353,384 filed 15th April, 1919, I have described the employment as high boiling plasticizing solvents for cellulose acetate, of high boiling mixtures of isomeric xylene 'low-carbon-alkyl sulphonamides, which mixtures are liquid at ordinary temperature, and are such as can be obtained by treating an ordinary commercial, xylene containing 0, m and p-xyle'nes, by the ordinary methods of conversion into the alkyl sulphonamides,

down to low temperature, this latter being:

for example by treating thecrude xylene mixed sulphochlorid'es with amines such as methlyamine, ethylamine,'etc.

., In the 1s: cification of another U. s.- Patent 'No.'-.1,33, 385 filed 15th A ril, r919, I have described the employment as high boilin'g plasticizing solventsfor cellulose ace tate, of "high boiling mixtures containing ortho and para toluene low-carbon-alkyl sulphonamides, which mixtures areliquid at ordinary temperature and. are such as, can

be obtained on treating commercial toluene,

by the ordinary methods of conversion into -the alkyl sulphonamides, for example bytreating the toluene with chlorosulphonic acid to form the corresponding sulphochlorides, treating the resulting raw mixture With ammonia .to convert the sulphochlorides into sulphon'amides, and then mythylating or ethylating to the monomethyl or monoethyl stage; or by treating the said raw mixture with amines such as methylamine, ethylamine, etc.

The present invention is characterized by the employment as plasticizing agents for the purpose mentioned, of high boiling mixtures of certain isomeric xylene low carbon dialkyl sulfonamides, being sulfonamides whereof at least one of the alkyl groups is ethyl, which mixtures are liquids at ordi nary temperature and are further character ized by forming jellies at temperatures considerably below ordinary room temperatures, v1z:- (a) Mixturespof isomeric xylene diethyl sulfonamides. Such mixtures boil at about 148-154 C. under 1 mm. pressure, are

'liquidat ordinary temperature, andform a soft clear jelly at 5 jelly at --20 C. r

(b) Mixtures of isomeric xylene mythyl ethyl sulfonamides. Such mixtures boil at about 155156 C. under 1 mm'., are liquid at ordinary temperature, form clear soft jeland a firm clear lies at 14: C; and slightly harder jellies at 20 O. A It has been found that for some applica $1,353,385 or my U. 8. Patent No. 1,501,206,

granted July 15, 1924, on application S. No.

' 401,380 filed August 5,1920, as their cellulose acetate solutions tend to become somewhat turbid when cooled down to or below ordinary temperature. Where this is not objectionable they may even be used alone, but they may be used together with the monoalkylated sulfonamide derivatives of my said specifications 1,353,384 and 1,353,385 or my Patent No. 1,501,206 of which the present is divisional, to obtain solutions. -wh1ch remain clear when cooled down, or

together with any other suitable high boilingsolvents-of cellulose acetate. I

Forpreparing the said mixtures of isomeric diethylor meythl ethyl sulfona-mides an ordinary commercial xylene was used in distilling between 135 and 146 C. (about 78% between 135 and 139 C.)

I do not, however, confine myself to working with these particular grades of hydrocarbon. c i

The procedure followed for preparing the alkyl sulfonamide products of the present invention may be according to the ordinary methods of preparing such alkylated compounds via the sulfochlorides, these either being treated with ammonia and then alkylated with the appropriate alkylating agents such as ethyl sulfuric acid salt or chlorethyl, or dimethyl sulfate, etc., or being treated direct with amines such as ethylamine, methylamine, etc.

It will be understood that in using the commercial impure xylene for making the mixtures of isomeric xylene diethylor methyl-ethyl sulfonamides as above mentioned, the treatment was carried out 'thereon without separation or purification of the intermediate or final products, though I do not confinemyself in this re ect, and it is to be understood that I do not limit myself to the particular procedure indicated for the preparation of the xylene alkyl sulfonamides of the present invention and that any other methods giving substantially similar products may be employed.

The high boiling plasticising solvents of the present invention may be employed in any suitable proportions, such for example as those indicated in my .said specification Not 1,353,384.

Similarly to the alkylated sulfonamides specified in my said previous patents, the new solvents of the present invention may be employed with any usual or suitable sol-- vents or liquids of low boiling point; likewiseany other usual or suitable substances may be added, such as triphenyl phosphate, tricresylphosphate or similarly acting agents, or acid neutralizing aliphatic derivatives of'urea which are liquid or have a low melting point, such as mono-, dior tri-methyl urea or mono-, dior tri-ethyl urea and so forth.

Also in making the solutions, compositions, or preparations with the solvents of the present invention any of the high boiling solvents of my U. S. PatentsNo. 1,501,206, dated July 15, 1924, or No. 1,508,928, dated Sept. 16, 1924, divisional thereof, may be added, or any other high boiling solvents or softening or plasticising substances may be added which are liquid substances, or even solid substances, provided they give liquid, gelatinous or non-solid mixtureswith the solvents of the invention.

In order to illustrate by way of example how the invention maybe carried out in practice, one may use to kilos of a highly viscous cellulose acetate, about 25 kilos of any of the xylene alkyl sulfonamide derivatives of the present invention or of mixtures of them, or of any of them with akyl sulfonamide derivatives of my said previous specifications, and about 12 kilos of tricresylphosphate or triphenylphosphate, these substances being mixed together with solvents of low boiling point such as acetone, methyl acetate or ethyl acetate mixed with alcohol (four volumes to one volume of al cohol), the mass being worked in the ordinary way in celluloid apparatus, first in the mixers, then on the rollers and afterwards in the presses, and so on, as generally practised in the celluloid industry. This gives quite a hard incombustible celluloid-like product.

The quantity of about 25 kilos of the alkyl sulfonamide solvents may be reduced together with that of the triphenylphosphate or tricresylphosphate in order to get a still harder product if desired.

()n the. other hand, by increasing this quantity of the sulfonamide solvents one gets softer products in proportion as the quantity is increased until a product is obtained which is pliable like a fabric.

For example, if one takes to 100 kilos of cellulose acetate about 100 kilos of one of the high boiling plasticising solvents of the present invention (or of a mixture of them) then one gets the kind of product which is pliable like a fabric, and if the plasticising solvent is employed in quantities less than 100 per cent, reckoned on the weight of the cellulose acetate, a proportionately stifferthe cellulose acetate the which can be used, and the less the Viscosity of the cellulose acetate the smaller the quan-" tity of the high boiling plasticising solvent which can be used.

Colouring matters, filling materials and any other usual or suitable materials such as commonly employed in the art may of course be added in making solutions, compositions or other products according to the invention. I

What I claim and desire to ters Patent is 1. A composition of matter containing cellulose acetate and a mixture of isomeric xylene low carbon dialkyl s'ulfonamides, being sulfonamides whereof at least one of secure by Letthe alkyl groups is ethyl which mixture is eater the quantity of the high boiling p asticising solvent liquid at ordinary temperature and forms a jelly at low temperatures.

2. A composition of matter comprising cellulose acetate and a plasticising agent comprising a mixture of isomeric low carbon dialkyl sulfonamides, being sulfonamides whereof at least one of the alkyl groups is ethyl, which mixture is liquid at ordinary room temperature and is a jelly at temperatures somewhat below 0 C.

3. A composition of matter comprising cellulose acetate and a plasticising agent comprising a mixture of isomeric diethyl sulfonamides, which mixture is liquid at ordinary room temperature and is a jelly at temperatures somewhat below 0 C. y

In testimony whereof I have hereunto subscribed my name.

HENRY DREYFUSv 

